Territory Account Executive - Winnipeg

The Role

At Square, we’re re‑imagining how small and midsize businesses grow. As a Sales Account Executive on our Outbound Team, you’ll bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You’ll run sophisticated, multi‑product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

Location

Winnipeg

Responsibilities

• Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and mid‑market merchants.


• Build and manage a high‑quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.


• Develop multi‑product solutions across Square’s ecosystem and tailor them to each merchant's unique needs.


• Conduct high‑impact discovery, demos, and negotiations wit...